Scottie Pippen
Best known as Michael Jordan’s right-hand man, Scottie Pippen was an integral part of the Chicago Bulls’ unstoppable 1990s. During this time, he spent nearly all of his $120 million on extravagent purchases. He even bought a private jet for $4 million, only to spend $1 million more when the jet didn’t work. Pippen even invested $20 with a fraudulent adviser, who was sentenced to prison in 2016.